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5 lessons from Shopify, Duolingo, and Fiverr going all in on AI
Ash + Lizzy
May 10, 2025
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Shopify, Duolingo, and Fiverr.
What do they have in common? They’re all in on AI.
Each company took a strikingly similar route to announce their bet-the-farm commitments to automation and efficiency: memos from the CEOs, alerting their teams that they’re now AI-first.
Shopify employees must now prove AI can't do the work before requesting headcount.
Duolingo is actively phasing out human contractors.
Fiverr said bluntly: “AI is coming for your jobs.”
They’re bold statements—and from a comms perspective, they paid off. All three announcements were widely covered in Tier 1 publications and the brands cemented themselves as leaders at the forefront of the AI transition.
But just as important as what they said was how they said it: screenshots of internal emails, shared directly from the CEO, with no couching or softening language.
It’s an effective strategy and we expect we’ll only see more founders skipping press releases in favor of announcing news via screenshots on X.
If you’re thinking about leveraging this strategy to make an announcement of your own, here’s what these companies got right and what you’ll want to watch out for to make sure you’re not just making headlines but actually moving the narrative forward.
1. Build up the founder’s brand.
If you need another reason to invest in your CEO’s brand, let this be it.
Shopify, Duolingo, and Fiverr are all household names, so attention was guaranteed. But how the messages landed varied—and it often came down to the strength of the executive delivering it. Watching the commentary online, Shopify’s memo in particular hit harder because Tobi Lütke has spent years cultivating a distinct public persona: decisive, technical, future-focused. These announcements hit differently when they come from a founder people trust. If you want your next big message to land, don’t just build a corporate brand—build a visible, consistent, trusted founder brand too.
2. Prepare for backlash and have a “why”
Big moves spark big reactions, especially when you’re touching third-rail topics like AI taking jobs. Duolingo’s memo, for example, sparked major backlash online. Will it meaningfully hurt their bottom line? Probably not. But it did muddy the coverage of their next big launch (150 new courses)—and shifted attention away from the product toward broader trust questions.
If you’re going to announce a bold pivot, make sure you have a clear, defensible "why" that internal and external audiences can rally around. Not everyone will love it, and that’s okay. But always prepare for scrutiny, confusion, and skepticism.
3. Pair it with an in-depth interview.
If you’re making a major strategic shift, don’t leave it at a screenshot of a memo—give yourself a second act. A week after Shopify’s internal memo went public, President Harley Finkelstein sat down with TBPN to discuss the strategy in more depth. It was effective, but if they had timed that interview to hit the same day, they may have been able to amplify their core message and avoid some of the backlash.
If you’re going direct, think about which channels you’ll use to reinforce your message and how to tell your whole story in a nuanced way.
4. Follow up with results
Bold announcements create expectations; the real credibility comes after. A memo or a screenshot can win you a news cycle—but what wins trust is showing visible, fast progress against what you promised. If you declare you’re going AI-first, you need clear signals that things are actually changing: new product launches, new team structures, measurable impact.
And don’t just share the wins—share the lessons. A transition like this won’t be smooth sailing. If you can find ways to share what you’re learning, you'll build trust and be seen as a true guide into this next shift.
5. Beware of AI messaging fatigue
The first few “we’re all in on AI” announcements made headlines. The ones that follow will land with a lot less force.
AI is still a narrative accelerant—but users are already starting to tire of it, and full-on backlash may not be far behind. If you’re going to lean into AI, tie it to something real: how your product will get better, how your users will benefit, why moving faster toward your mission actually matters and why AI is the right tool to get you there.
📱 New in non-traditional media
Tracking the newsletters, podcasts, and creators reshaping media influence.
📰 In the news
More TechCrunch exits
Veteran reporters Paul Sawers and Ingrid Lunden are leaving TechCrunch, continuing a steady wave of high-profile departures. The old guard of startup media is thinning—and many are betting on independent platforms.Golden Globes adds podcast category
The Golden Globes are launching a new award for Best Podcast in 2026, citing “the growing influence and reach of podcasts in the entertainment industry”. It’s a signal that long-form audio is now accepted as mainstream entertainment.Axios picks up Ryan Barwick
From one major newsletter to another, Axios has hired Ryan Barwick—formerly of Morning Brew—to cover dealmaking for Axios Pro.
🎤 Spotlight on neurotech creators
With the tariffs upon us, supply chain experts have a lot to say. If you’re building in supply chain tech, here are a few non-traditional media outlets to keep on your radar:
Delivers curated updates, research highlights, and analysis on neurotechnology
Edited by Robert Murcko, it covers topics like non-invasive neural interfaces, funding news, and emerging trends in neurotech.
Companion podcast
Trade publication and newsletter tracking clinical and commercial BCI developments
Go-to source for coverage on implantables, neurostimulation, and emerging players
Also runs the annual Neurotech Leaders Forum
Hosted by Paul Middlebrooks
Explores the intersection of neuroscience and artificial intelligence and how the brain can inform the development of intelligent systems
Features discussions with researchers, engineers, and thought leaders.
Hosted by Ladan Jiracek
Brings together the field of neuroprosthetics, brain-machine interfaces, and brain implants through accessible conversations about current topics and breakthroughs.
⭐️ Favorite story of the week:
If you write for real, ChatGPT cannot replace you - House of Strauss
“When the Celtics lose, I want to hear from Bill Simmons, just to see how Bill Simmons specifically reacts. I don’t care if a machine might give me a more objective and comprehensive take on Jayson Tatum. I want the biased human version, informed by years of memories.”
Strauss was talking about sports, but the same logic applies to founders. AI can summarize the facts. What it can’t do is recreate your instincts, hard-won lessons, or specific way of seeing the world. Build your brand so people want your take—not just the information.
⚡️ Steal this pitch
Here’s a real pitch we used to land press coverage using newly released data:
Subject: AI-Powered Cybercrime: Are Organizations Ready for 2025?
Pitch:
In the past year, 87% of global organizations have faced AI-powered attacks (according to SoSafe’s Cybercrime Trends Report), with cybercriminals now deploying deepfake voice calls, AI-generated video messages, and hyper-personalized phishing across multiple platforms. While organizations become more aware of these threats, most still express limited certainty in their ability to detect and respond to these rapidly-evolving threats.
Proactive strategies-like implementing Software Bill of Materials (SBOMs) and Vulnerability Exploitability eXchange (VEX) files-are critical for managing vulnerabilities and securing the software supply chain. These tools provide transparency, automate risk identification, and help teams stay ahead of attackers leveraging AI for constant adaptation.
[EXECUTIVE] of [COMPANY], is available to discuss how organizations can build true cyber resilience in the age of AI. He can provide insight on:
How AI is transforming the threat landscape right now
Why traditional defenses are falling short
Lessons learned from real-world attacks and open-source security initiatives
💫 Client wins
Our clients are making headlines. Check out coverage our clients got this week in Carbon Herald, Carbon Pulse, and the Wired for Wonder pod.
Want coverage like this? Say hello.
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